Dichloromethane → HCID 22961979, compound

HRID 389111Notes

Reaction equation

HRID 389111 reaction equation
C(N(CC)CC)C.Cl[C:9]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[NH:28]1[C:32]2[CH2:33][CH2:34][CH:35]([C:37]([O:39][CH3:40])=[O:38])[CH2:36][C:31]=2[N:30]=[CH:29]1.ClCCl>O>[C:9]([N:28]1[C:32]2[CH2:33][CH2:34][CH:35]([C:37]([O:39][CH3:40])=[O:38])[CH2:36][C:31]=2[N:30]=[CH:29]1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178497375HCID 178497375, compound

Product 1

HCID 22961979HCID 22961979, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Triethylamine (4.7 ml) and chlorotriphenylmethane (9.37 g) were added to a mixture of methyl 4,5,6,7-tetrahydro-1H-benzimidazole-5-carboxylate (6.73 g) and dichloromethane (70 ml), followed by stirring at room temperature overnight. Water was added to the reaction solution, followed by extraction with dichloromethane, the organic layer was concentrated, and the resulting residue was purified by silica gel column chromatography (chloroform) to obtain a mixture (10.13 g) of methyl 1-trityl-4,5,6,7-tetrahydro-1H-benzimidazole-5-carboxylate and methyl 1-trityl-4,5,6,7-tetrahydro-1H-benzimidazole-6-carboxylate. Methanol (50 ml), water (20 ml) and sodium hydroxide (4.78 g) were added to the obtained mixture, followed by heating to reflux overnight. The reaction solution was concentrated, water and concentrated hydrochloric acid (8 ml) were added to the residue, and the precipitated solid was collected by filtration, washed with water and acetone and dried under reduced pressure to obtain a mixture (7.07 g) of 1-trityl-4,5,6,7-tetrahydro-1H-benzimidazole-5-carboxylic acid and 1-trityl-4,5,6,7-tetrahydro-1H-benzimidazole-6-carboxylic acid, as a colorless solid.

Workup

  1. extractionfollowed by extraction with dichloromethane
  2. concentrationthe organic layer was concentrated
  3. customthe resulting residue was purified by silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-2addf12291174ee58c34b9e86e2e959a
Source dataset
uspto-grants-2013_02
Patent number
US08377923B2

Reaction notes

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